214360-63-1

Basic information

• Product Name: 2-(4-methoxy-3-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• Synonyms: 2-(3-Methyl-4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-(4-methoxy-3-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS NO: 214360-63-1
• Molecular Formula: C₁₄H₂₁BO₃
• Molecular Weight: 248.13
• Mol File: 214360-63-1.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-(4-methoxy-3-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-methoxy-3-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(214360-63-1)
• EPA Substance Registry System: 2-(4-methoxy-3-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(214360-63-1)

Safety Data

• Hazardous Substances Data: 214360-63-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2-(4-methoxy-3-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is used as a reagent for the formation of carbon-carbon and carbon-heteroatom bonds in organic synthesis. Its ability to participate in cross-coupling reactions, such as Suzuki and Stille couplings, makes it a valuable component in the synthesis of complex organic molecules.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 2-(4-methoxy-3-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is used as a building block for creating complex molecular structures. Its versatility in forming various chemical bonds allows for the development of new pharmaceutical compounds with potential therapeutic applications.

Upstream product

• 75581-11-2 1-iodo-4-methoxy-3-methylbenzene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 14804-31-0 2-methyl-4-bromoanisole 
• 73183-34-3 bis(pinacol)diborane 
• 3260-85-3 2-methyl-4-chloroanisole 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 578-58-5 2-methylmethoxybenzene 

Downstream Products

• 1276544-74-1 7-chloro-3-(2-chloro-4-fluorobenzyl)-5-(4-methoxy-3-methylphenyl)-1-(4-methoxybenzyl)-1H-benzo[e][1,4]diazepin-2(3H)-one 

Relevant articles and documents

Para -C-H borylation of benzene derivatives by a bulky iridium catalyst

A highly para-selective aromatic C-H borylation has been accomplished. By a new iridium catalyst bearing a bulky diphosphine ligand, Xyl-MeO-BIPHEP, the C-H borylation of monosubstituted benzenes can be affected with para-selectivity up to 91%. This catalytic system is quite different from the usual iridium catalysts that cannot distinguish meta- and para-C-H bonds of monosubstituted benzene derivatives, resulting in the preferred formation of meta-products. The para-selectivity increases with increasing bulkiness of the substituent on the arene, indicating that the regioselectivity of the present reaction is primarily controlled by steric repulsion between substrate and catalyst. Caramiphen, an anticholinergic drug used in the treatment of Parkinsons disease, was converted into five derivatives via our para-selective borylation. The present [Ir(cod)OH]2/Xyl-MeO-BIPHEP catalyst represents a unique, sterically controlled, para-selective, aromatic C-H borylation system that should find use in streamlined, predictable chemical synthesis and in the rapid discovery and optimization of pharmaceuticals and materials.

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Method for preparing aminoarylborane compounds or derivatives thereof

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The synthesis of arylboronic ester derivatives from aryl chlorides by using aryl(amino)boranes is described. Palladium-catalyzed coupling between aryl chlorides and diisopropylaminoborane leads to the formation of a C-B bond under mild conditions. A wide range of functional groups are tolerated, making this method particularly useful for the borylation of functionalized aromatics. Salts make the difference: The synthesis of arylboronic ester derivatives from aryl chlorides by using aryl(amino)boranes is described. Palladium-catalyzed coupling between aryl chlorides and diisopropylaminoborane leads to the formation of a C-B bond under mild conditions. A wide range of substituents, including electron-withdrawing groups, are tolerated (see scheme).

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